Best Podcast Episodes About Khosla Ventures
Everything podcasters are saying about Khosla Ventures — curated from top podcasts
Updated: Apr 26, 2026 – 5 episodes
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Ridealong has curated the best and most interesting podcasts and clips about Khosla Ventures.
Top Podcast Clips About Khosla Ventures
“… Officer at Square, VP of Corporate Development at LinkedIn. He's also co-founded two companies, and he's currently Managing Director at Kostla Ventures. It's safe to say that Keith is in the 99.9th percentile at Identifying Talent, Building Teams, and Operating World-Class Companies. Before we get into it, don't forget to check out Lenny's Product Pass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. With that, I bring you Keith Raboy. Keith, thank you so much for being here and welcome to the podcast. It's a pleasure to be with you. Okay, so when we …”
“… He was an early investor in Stripe, Palantir, Airbnb, YouTube, DoorDash, Ramp, and dozens of other companies. He's part of the famous PayPal Mafia, where he was Executive Vice President of Business Development and Policy. He's also been Chief Operating Officer at Square, VP of Corporate Development at LinkedIn. He's also co-founded two companies, and he's currently Managing Director at Kostla Ventures. It's safe to say that Keith is in the 99.9th percentile at Identifying Talent, Building Teams, and Operating World-Class Companies. Before we get into it, don't forget to check out Lenny's Product Pass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. With that, I bring you Keith Raboy. Keith, thank you so much for being here and welcome to the podcast. It's a pleasure to be with you. Okay, so when we were starting this recording, you told me you're doing this from an iPad, which I've never had. And you shared a crazy fact that you haven't used a computer in like years. Talk about what's going on there. Yeah, so when I started working at Square, Jack Dorsey was running the company off an iPad And so I immediately converted in September 2010 and …”
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Keith Rabois, a tech industry titan, hasn't used a computer since 2010, opting instead for an iPad to boost productivity and minimize distractions. His unique approach not only reflects a personal preference but also aligns with a growing trend of engineers coding from their phones. This shift highlights how technology can enhance flexibility in work environments.
“… interesting raise from a company we've all likely encountered on Zoom calls. AI note-taking startup Granola has raised $125 million led by Index Ventures at a $1.5 billion valuation and plans Claude integrations and agentic AI features in the next year. Quoting Bloomberg, Granola's product transcribes conversations and uses AI to turn rough draft meeting notes into complete summaries. Chief Executive Officer Chris Pedregal said that many of its corporate customers, which include companies like Cursor and Gusto, have adopted the technology after individual employees started using it. Something …”
“Finally today, interesting raise from a company we've all likely encountered on Zoom calls. AI note-taking startup Granola has raised $125 million led by Index Ventures at a $1.5 billion valuation and plans Claude integrations and agentic AI features in the next year. Quoting Bloomberg, Granola's product transcribes conversations and uses AI to turn rough draft meeting notes into complete summaries. Chief Executive Officer Chris Pedregal said that many of its corporate customers, which include companies like Cursor and Gusto, have adopted the technology after individual employees started using it. Something similar happened at Index, Reimer said. Multiple people at the firm were using the technology by the time he considered investing. Alongside the funding, the startup is launching new features for its app, including integrations with AI coding tools like Anthropics Claude Code, as well as team workspaces where employees can pull their notes. Granola's …”
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AI note-taking startup Granola just raised $125 million, reaching a $1.5 billion valuation, to enhance its features with Claude integrations and agentic AI capabilities. With existing corporate clients like Cursor and Gusto, Granola is set to redefine how teams collaborate using AI, moving beyond simple note-taking into a more dynamic workspace. CEO Chris Pedregal emphasizes that they are just beginning to explore the potential of AI in work collaboration.
“… capital raise which is the pre round that we have So we only have one prior capital race which is the accelerator round that we did with Forum Ventures and Rise Forum Ventures has an accelerator in San Francisco Awesome to know. We'll make a note of that so we can trade deal flow. And what makes you, last question,”
“… in SF. Have you gone through any of the accelerators yet? Have you raised capital before? Tell us a little bit about the history of the company. Yeah. So, obviously, great to walking through this, coming around with you guys as we're wrapping our second capital raise which is the pre round that we have So we only have one prior capital race which is the accelerator round that we did with Forum Ventures and Rise Forum Ventures has an accelerator in San Francisco Awesome to know. We'll make a note of that so we can trade deal flow. And what makes you, last question,”
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Deploying energy-saving technology is a multi-million dollar challenge for startups. Many companies struggle to get big brands to commit due to slow-moving processes and high costs. However, with a scalable model and a quick pilot phase, startups can prove ROI and potentially revolutionize energy efficiency in large portfolios.
“… there as well. And she is the most qualified. I think she was on the search team. She was a VP in Google on the search team. She was at Gradient Ventures. And so it's going to be interesting to see what she has to say. I'm going to pull her up right now. And hi, Anna. Good morning. Hi. Good morning. Great to see you. And great to have you on the show. while we were preparing for the show, we were asking ourselves, why is low-cost search so important right now? Why this idea of bringing down the search cost is so important, and you are pushing forward this idea of five cents per 1,000 queries. …”
“… five cents per 1 search queries So they doing industrial volumes of search queries I think they in a space I think we've seen Exa in a similar space, Parallels, the company formed by the former Twitter CEO. I think there are a couple of other people there as well. And she is the most qualified. I think she was on the search team. She was a VP in Google on the search team. She was at Gradient Ventures. And so it's going to be interesting to see what she has to say. I'm going to pull her up right now. And hi, Anna. Good morning. Hi. Good morning. Great to see you. And great to have you on the show. while we were preparing for the show, we were asking ourselves, why is low-cost search so important right now? Why this idea of bringing down the search cost is so important, and you are pushing forward this idea of five cents per 1,000 queries. Why is that important? I think, you know, I was so excited about the GPT 5.5 job. One of the things that you is, you know, that a lot of people don't know is the second a model is released, it's already stale because the training for that model was months ago. So kind of search together with AI models is is here to stay so that you wouldn't hire an …”
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Low-cost search at just five cents per 1,000 queries could revolutionize how AI models access real-time information. Anna Patterson from Ceramic AI explains that traditional search costs have hindered the development of smaller, efficient models. By making search affordable and fast, we can enhance the reliability of AI systems, particularly in critical applications like legal tech.
“… had to bet on two or three things that you're doing right now where you're going to get the biggest payday? What are they? Well, power. So Outlaw Ventures, we power digital infrastructure. So I sell power to data centers. And so my last project raised $150 million to build a substation. And so we recently just sold that. It's a Google-backed partnership. And that was amazing. I've got a lot more of those sites. And I'm taking the same playbook, bro, that I did in the home service industry, and I'm building it out in the power industry, smart outbound. And so outlaw ventures, definitely that I …”
“… placed where the biggest monetary gains that you've seen the next five years for yourself would be it sounds like by the way i i can go on and on about my investments and stuff yeah you know i'm not i'm not calling you out i'm just asking you if you had to bet on two or three things that you're doing right now where you're going to get the biggest payday? What are they? Well, power. So Outlaw Ventures, we power digital infrastructure. So I sell power to data centers. And so my last project raised $150 million to build a substation. And so we recently just sold that. It's a Google-backed partnership. And that was amazing. I've got a lot more of those sites. And I'm taking the same playbook, bro, that I did in the home service industry, and I'm building it out in the power industry, smart outbound. And so outlaw ventures, definitely that I love roof fix and the technology that we have there. And the opportunity that I see, because this is a pretty difficult end. I feel like roofing, everyone's like, Oh, it's so easy. It's like, no, it's not. Whenever you really, there's a lot of variables that come into play. And it's not just like service completion. There's insurance, mortgage claims, …”
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The roofing industry is ripe for transformation as it faces challenges like unpredictability and bad actors. Josey Parks, a tech entrepreneur, sees immense opportunity in bringing professionalism and technology to this fragmented field. By leveraging innovation, he aims to maximize leads and streamline operations in an industry often misunderstood as simple.
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